AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD

AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD

A Derivatives of 2-thiouracil are characteri­zed by wide spectrum of biological activity, which is characteristic of most representatives this heterocycles class. In particular, 2-(2-oxo-2-phenylethylthio)-pyrimi­din-4(3H)-ones belong to the group of non-nucleoside inhibitors of HIV-1 reverse transc...

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Datum:2023
Hauptverfasser: Yavolovskii, Arkadii, Davtian, Araksia, Grishchuk, Lidiya, Pluzhnik-Glagyr, Sergei, Rakipov, Ildar, Ivanov, Yuri, Chikhichin, Dmytro, Kamalov, Gerbert
Format: Artikel
Sprache:English
Veröffentlicht: V.I.Vernadsky Institute of General and Inorganic Chemistry 2023
Online Zugang:https://ucj.org.ua/index.php/journal/article/view/518
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Назва журналу:Ukrainian Chemistry Journal

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Ukrainian Chemistry Journal
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spelling oai:ojs2.1444248.nisspano.web.hosting-test.net:article-5182023-04-18T13:56:31Z AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD Yavolovskii, Arkadii Davtian, Araksia Grishchuk, Lidiya Pluzhnik-Glagyr, Sergei Rakipov, Ildar Ivanov, Yuri Chikhichin, Dmytro Kamalov, Gerbert 2-(2-oxo-2-phenylethylthio)-py­ri­midines, amination, sulfonate method. A Derivatives of 2-thiouracil are characteri­zed by wide spectrum of biological activity, which is characteristic of most representatives this heterocycles class. In particular, 2-(2-oxo-2-phenylethylthio)-pyrimi­din-4(3H)-ones belong to the group of non-nucleoside inhibitors of HIV-1 reverse transcriptase. The antimalarial properties of 2-(2-oxo-2-phenylethyl­thio)-4-R-pyrimidine derivatives, which proved to be effective inhibitors of CIpP protease of Plasmodium falciparum, are being studied. Known examples of 2-(2-oxo-2-phenylethyl­thio)-pyrimidines modification at the "4" position of the heterocycle are limited to use 4-chloro derivatives, which, in turn, are formed according to the classical method by reaction of pyrimidine-4(3H)-ones with POCl3 at boiling point of reaction mixture. In this work, we present an alternative version of modification the above-mentioned class of compounds. By amination amide function of 6-R-2-(2-oxo-2-arylethylthio)-pyrimidin-4(3H)-ones derivati­ves of with ethanolamine and 1-aminopropa­ne-2,3-diol using sulfonate method, synthesized and characterized new compounds a 6-R-2-(2-oxo-2-phenylethylthio)-pyrimidines series by spectral methods. The advantages of this scheme are discussed (the formation of intermediate sulfonates and the amination stage do not require harsh conditions and are carried out with satisfactory yields). The proposed scheme can be recommended in cases where the original substrate contains functio­nal groups that are labile at high temperatures and sensitive to an acidic environment. V.I.Vernadsky Institute of General and Inorganic Chemistry 2023-02-24 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/518 10.33609/2708-129X.89.01.2023.60-67 Ukrainian Chemistry Journal; Vol. 89 No. 1 (2023): Ukrainian Chemistry Journal; 60-67 Украинский химический журнал; Том 89 № 1 (2023): Ukrainian Chemistry Journal; 60-67 Український хімічний журнал; Том 89 № 1 (2023): Український хімічний журнал; 60-67 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/518/265
institution Ukrainian Chemistry Journal
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datestamp_date 2023-04-18T13:56:31Z
collection OJS
language English
topic_facet 2-(2-oxo-2-phenylethylthio)-py­ri­midines
amination
sulfonate method.
format Article
author Yavolovskii, Arkadii
Davtian, Araksia
Grishchuk, Lidiya
Pluzhnik-Glagyr, Sergei
Rakipov, Ildar
Ivanov, Yuri
Chikhichin, Dmytro
Kamalov, Gerbert
spellingShingle Yavolovskii, Arkadii
Davtian, Araksia
Grishchuk, Lidiya
Pluzhnik-Glagyr, Sergei
Rakipov, Ildar
Ivanov, Yuri
Chikhichin, Dmytro
Kamalov, Gerbert
AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
author_facet Yavolovskii, Arkadii
Davtian, Araksia
Grishchuk, Lidiya
Pluzhnik-Glagyr, Sergei
Rakipov, Ildar
Ivanov, Yuri
Chikhichin, Dmytro
Kamalov, Gerbert
author_sort Yavolovskii, Arkadii
title AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
title_short AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
title_full AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
title_fullStr AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
title_full_unstemmed AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
title_sort amination of 2-(2-oxo-2-arylethylthio)-pyrimidin-4(3h)-one derivatives using the sulfonate method
description A Derivatives of 2-thiouracil are characteri­zed by wide spectrum of biological activity, which is characteristic of most representatives this heterocycles class. In particular, 2-(2-oxo-2-phenylethylthio)-pyrimi­din-4(3H)-ones belong to the group of non-nucleoside inhibitors of HIV-1 reverse transcriptase. The antimalarial properties of 2-(2-oxo-2-phenylethyl­thio)-4-R-pyrimidine derivatives, which proved to be effective inhibitors of CIpP protease of Plasmodium falciparum, are being studied. Known examples of 2-(2-oxo-2-phenylethyl­thio)-pyrimidines modification at the "4" position of the heterocycle are limited to use 4-chloro derivatives, which, in turn, are formed according to the classical method by reaction of pyrimidine-4(3H)-ones with POCl3 at boiling point of reaction mixture. In this work, we present an alternative version of modification the above-mentioned class of compounds. By amination amide function of 6-R-2-(2-oxo-2-arylethylthio)-pyrimidin-4(3H)-ones derivati­ves of with ethanolamine and 1-aminopropa­ne-2,3-diol using sulfonate method, synthesized and characterized new compounds a 6-R-2-(2-oxo-2-phenylethylthio)-pyrimidines series by spectral methods. The advantages of this scheme are discussed (the formation of intermediate sulfonates and the amination stage do not require harsh conditions and are carried out with satisfactory yields). The proposed scheme can be recommended in cases where the original substrate contains functio­nal groups that are labile at high temperatures and sensitive to an acidic environment.
publisher V.I.Vernadsky Institute of General and Inorganic Chemistry
publishDate 2023
url https://ucj.org.ua/index.php/journal/article/view/518
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